5-(3-((4,6-dioxo-3-phenyl-2-thioxo-tetrahydropyrimidin-5(6H)-ylidene)methyl)-2,5-dimethyl-1H-pyrrol-1-yl)isophthalic acid

ID: ALA562422

Chembl Id: CHEMBL562422

PubChem CID: 2279009

Max Phase: Preclinical

Molecular Formula: C25H19N3O6S

Molecular Weight: 489.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(/C=C2/C(=O)NC(=S)N(c3ccccc3)C2=O)c(C)n1-c1cc(C(=O)O)cc(C(=O)O)c1

Standard InChI:  InChI=1S/C25H19N3O6S/c1-13-8-15(14(2)27(13)19-10-16(23(31)32)9-17(11-19)24(33)34)12-20-21(29)26-25(35)28(22(20)30)18-6-4-3-5-7-18/h3-12H,1-2H3,(H,31,32)(H,33,34)(H,26,29,35)/b20-12-

Standard InChI Key:  JQIGYUULGQKILM-NDENLUEZSA-N

Alternative Forms

1. Parent:

   

   ALA562422

   5-[3-[(Z)-(4,6-dioxo-1-phenyl-2-sulfanylidene-1,3-diazinan-5-ylidene)methyl]-2,5-dimethylpyrrol-1-yl]benzene-1,3-dicarboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 489.51

Molecular Weight (Monoisotopic): 489.0995

AlogP: 3.32

#Rotatable Bonds: 5

Polar Surface Area: 128.94

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.44

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: -2.58

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: -1.44

References

1. Perdih A, Kovac A, Wolber G, Blanot D, Gobec S, Solmajer T..  (2009)  Discovery of novel benzene 1,3-dicarboxylic acid inhibitors of bacterial MurD and MurE ligases by structure-based virtual screening approach.,  19  (10): [PMID:19369074] [10.1016/j.bmcl.2009.03.141]

2. Perdih A, Hrast M, Barreteau H, Gobec S, Wolber G, Solmajer T..  (2014)  Benzene-1,3-dicarboxylic acid 2,5-dimethylpyrrole derivatives as multiple inhibitors of bacterial Mur ligases (MurC-MurF).,  22  (15): [PMID:24953950] [10.1016/j.bmc.2014.05.058]

Source

Source(1):

• Scientific Literature